A fungal metabolite
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Aspergillimide

Item No. 27738

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3'R,5aR,8aR,9aS)-rel-(-)-tetrahydro-1,1',8,8,11-pentamethyl-spiro[5H,6H-5a,9a-(iminomethano)-1H-cyclopent[f]indolizine-7(8H),3'-pyrrolidine]-2',5',10-trione
CAS Number
195966-93-9
Synonyms
  • Asperparaline A
  • VM 55598
Molecular Formula
C20H29N3O3
Formula Weight
359.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C(C1)N(C)C([C@@]21C(C)(C)[C@]3([H])CC45N(CC[C@@H]4C)C[C@]3(N(C)C5=O)C2)=O
InChi Code
InChI=1S/C20H29N3O3/c1-12-6-7-23-11-19-10-18(9-14(24)21(4)15(18)25)17(2,3)13(19)8-20(12,23)16(26)22(19)5/h12-13H,6-11H2,1-5H3/t12-,13-,18-,19+,20?/m0/s1
InChi Key
RTNMRJRMTGSUAE-UXVBPGSQSA-N
Origin
Fungi/Aspergillus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Aspergillimide is a fungal metabolite originally isolated from A. japonicus.1 It reduces nicotinic acetylcholine receptor (nAChR) peak and slowly-desensitizing amplitudes induced by acetylcholine in silkworm (B. mori) larval neurons (IC50s = 20.2 and 39.6 nM, respectively) but has no effect on chicken α3β4-, α4β2-, and α7-containing nAChRs.2 Dietary administration of aspergillimide A (10 µg/g of diet) induces paralysis in silkworm fourth instar larvae.1 Aspergillimide A (10 and 20 mg/kg) reduces T. colubriformis fecal egg count in gerbils.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hayashi, H., Nishimoto, Y., Akiyama, K., et al. New paralytic alkaloids, asperparalines A, B and C, from Aspergillus japonicus JV-23. Biosci. Biotechnol. Biochem. 64(1), 111-115 (2000).

    2. Hirata, K., Kataoka, S., Furutani, S., et al. A fungal metabolite asperparaline a strongly and selectively blocks insect nicotinic acetylcholine receptors: The first report on the mode of action. PLoS One 6(4), e18354 (2011).

    3. Banks, R.M., Blanchflower, S.E., Everett, J.R., et al. Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides. J. Antibiot. (Tokyo) 50(10), 840-846 (1997).